JPH1036372A - 新規なピリダジノ−、ピリミド−、ピラジノ−およびトリアジノ−インドール類 - Google Patents

新規なピリダジノ−、ピリミド−、ピラジノ−およびトリアジノ−インドール類

Info

Publication number: JPH1036372A
Authority: JP; Japan
Prior art keywords: carbon atoms; straight; chain; substituted; branched
Prior art date: 1996-04-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP9106814A

Other languages

English (en)

Japanese (ja)

Inventor

Ulrich Dr Mueller

ウルリヒ・ミユラー

Peter Dr Eckenberg

ペーター・エツケンベルク

Rudi Dr Gruetzmann

ルデイ・グリユツツマン

Hilmar Dr Bischoff

ヒルマー・ビシヨフ

Dirk Dr Denzer

デイルク・デンツアー

Ulrich Dr Nielsch

ウルリヒ・ニールシユ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-04-18

Filing date

1997-04-10

Publication date

1998-02-10

1997-04-10 Application filed by Bayer AG filed Critical Bayer AG

1998-02-10 Publication of JPH1036372A publication Critical patent/JPH1036372A/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 79
125000000217 alkyl group Chemical group 0.000 claims abstract description 74
125000003545 alkoxy group Chemical group 0.000 claims abstract description 47
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 36
-1 (substituted) phenyl ring Chemical group 0.000 claims abstract description 35
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 31
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
150000002367 halogens Chemical class 0.000 claims abstract description 20
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
239000003814 drug Substances 0.000 claims abstract description 11
125000005842 heteroatom Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 150
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
150000002431 hydrogen Chemical class 0.000 claims description 33
239000000460 chlorine Substances 0.000 claims description 27
125000004076 pyridyl group Chemical group 0.000 claims description 27
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
229910052801 chlorine Inorganic materials 0.000 claims description 26
125000002252 acyl group Chemical group 0.000 claims description 25
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
125000003342 alkenyl group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
230000003213 activating effect Effects 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 4
150000001925 cycloalkenes Chemical class 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
230000009435 amidation Effects 0.000 claims description 3
238000007112 amidation reaction Methods 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
238000013329 compounding Methods 0.000 claims description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
230000000640 hydroxylating effect Effects 0.000 claims 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
201000001320 Atherosclerosis Diseases 0.000 abstract description 5
208000029078 coronary artery disease Diseases 0.000 abstract description 5
229940079593 drug Drugs 0.000 abstract description 3
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
208000019622 heart disease Diseases 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 25
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 25
229910052794 bromium Inorganic materials 0.000 description 25
238000000034 method Methods 0.000 description 25
239000000203 mixture Substances 0.000 description 23
239000011737 fluorine Substances 0.000 description 22
229910052731 fluorine Inorganic materials 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
239000000243 solution Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
241001465754 Metazoa Species 0.000 description 17
239000002904 solvent Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000003208 petroleum Substances 0.000 description 16
210000002966 serum Anatomy 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000002585 base Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 12
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
108010062497 VLDL Lipoproteins Proteins 0.000 description 11
230000007062 hydrolysis Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
230000008569 process Effects 0.000 description 9
239000000047 product Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 9
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000011734 sodium Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
239000008280 blood Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000002245 particle Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
238000012360 testing method Methods 0.000 description 7
241000416162 Astragalus gummifer Species 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
108090001030 Lipoproteins Proteins 0.000 description 6
102000004895 Lipoproteins Human genes 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
229920001615 Tragacanth Polymers 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
230000028327 secretion Effects 0.000 description 6
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
125000001544 thienyl group Chemical group 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
239000000196 tragacanth Substances 0.000 description 6
235000010487 tragacanth Nutrition 0.000 description 6
229940116362 tragacanth Drugs 0.000 description 6
150000003626 triacylglycerols Chemical class 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 5
239000004913 cyclooctene Substances 0.000 description 5
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
238000001035 drying Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000004006 olive oil Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
235000012000 cholesterol Nutrition 0.000 description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
239000003599 detergent Substances 0.000 description 4
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
238000005259 measurement Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
239000004033 plastic Substances 0.000 description 4
230000000291 postprandial effect Effects 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
208000008589 Obesity Diseases 0.000 description 3
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
239000012062 aqueous buffer Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000007423 decrease Effects 0.000 description 3
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 3
238000001952 enzyme assay Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
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OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
OCTNNXHKAOLDJL-BMGYQPLYSA-N Salbostatin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)OC[C@@H]1N[C@@H]1[C@H](O)[C@@H](O)[C@H](O)C(CO)=C1 OCTNNXHKAOLDJL-BMGYQPLYSA-N 0.000 description 1
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239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
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235000011087 fumaric acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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239000003547 immunosorbent Substances 0.000 description 1
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235000014655 lactic acid Nutrition 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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239000002184 metal Substances 0.000 description 1
FPHIJLWQUGAXRZ-UHFFFAOYSA-N methyl 2-[methyl(methylamino)carbamoyl]-1h-indole-3-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(C(=O)N(C)NC)NC2=C1 FPHIJLWQUGAXRZ-UHFFFAOYSA-N 0.000 description 1
GNKQWYILRWETDJ-UHFFFAOYSA-N methyl(methylamino)azanium;dichloride Chemical compound [Cl-].[Cl-].CN[NH2+]C.CN[NH2+]C GNKQWYILRWETDJ-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
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230000003000 nontoxic effect Effects 0.000 description 1
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230000004526 pharmaceutical effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229950001790 tendamistat Drugs 0.000 description 1
108010037401 tendamistate Proteins 0.000 description 1
JNXWYJWBRZOTAF-UHFFFAOYSA-N tert-butyl 2-(4-methylphenyl)acetate Chemical compound CC1=CC=C(CC(=O)OC(C)(C)C)C=C1 JNXWYJWBRZOTAF-UHFFFAOYSA-N 0.000 description 1
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

JP9106814A 1996-04-18 1997-04-10 新規なピリダジノ−、ピリミド−、ピラジノ−およびトリアジノ−インドール類 Pending JPH1036372A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19615265A DE19615265A1 (de)	1996-04-18	1996-04-18	Neue Pyridazino-, Pyrimido-, Pyrazino- und Triazino-indole
DE19615265.8		1996-04-18

Publications (1)

Publication Number	Publication Date
JPH1036372A true JPH1036372A (ja)	1998-02-10

Family

ID=7791600

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9106814A Pending JPH1036372A (ja)	1996-04-18	1997-04-10	新規なピリダジノ−、ピリミド−、ピラジノ−およびトリアジノ−インドール類

Country Status (5)

Country	Link
US (1)	US5786361A (fr)
EP (1)	EP0802198A3 (fr)
JP (1)	JPH1036372A (fr)
CA (1)	CA2202703A1 (fr)
DE (1)	DE19615265A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2003503342A (ja) *	1999-06-25	2003-01-28	バイエルアクチェンゲゼルシャフト	ＭＴＰ阻害剤とＨＭＧ−ＣｏＡ還元酵素阻害剤との組み合わせ並びに薬剤におけるその使用
JP2003535888A (ja) *	2000-06-21	2003-12-02	バイエルアクチェンゲゼルシャフト	食後のトリグリセリドに富んだリポタンパク質粒子（ｐｐｔｒｌ）の数を低下させるための、ミクロソームのトリグリセリド輸送タンパク質（ｍｔｐ）インヒビターの使用
WO2025239340A1 (fr) *	2024-05-14	2025-11-20	日本農薬株式会社	Composé amide ou sel de celui-ci, microbicide agricole et horticole contenant ledit composé ou sel, et procédé d'utilisation dudit microbicide

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Publication number	Priority date	Publication date	Assignee	Title
US6365586B1 (en) *	1998-10-21	2002-04-02	Novo Nordisk A/S	Compounds, their preparation and use
US20030077301A1 (en) *	1999-12-16	2003-04-24	Maibach Howard I.	Topical pharmaceutical composition for the treatment of inflammatory dermatoses
NZ549721A (en)	2004-03-05	2010-08-27	Univ Pennsylvania	Methods for treating disorders or diseases associated with hyperlipidemia and hypercholesterolemia while minimizing side-effects
JP2009511635A (ja) *	2005-10-18	2009-03-19	エージェリオンファーマシューティカルズ	哺乳動物における高脂血症に関連する障害を治療するための方法
US20080161279A1 (en) *	2006-12-21	2008-07-03	Wisler Gerald L	Methods of Treating Obesity
CA2737031A1 (fr)	2008-09-29	2010-04-01	Abbott Laboratories	Derives d'indole et d'indoline et procedes d'utilisation de ceux-ci
US9625475B2 (en)	2008-09-29	2017-04-18	Abbvie Inc.	Indole and indoline derivatives and methods of use thereof
EP4188372A1 (fr)	2020-07-29	2023-06-07	Amryt Pharmaceuticals Inc.	Lomitapide destiné à être utilisé dans des méthodes de traitement de l'hyperlipidémie et de l'hypercholestérolémie chez des patients pédiatriques

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IL81325A (en) *	1986-01-23	1990-11-29	Merck Frosst Canada Inc	Tetrahydrocarbazole 1-alkanoic acids and pharmaceutical compositions containing them
US4775680A (en) *	1987-07-21	1988-10-04	Merck & Co., Inc.	Cyclohept[b]indolealkanoic acids, pharmaceutical compositions and use
JPH01313480A (ja) *	1988-06-14	1989-12-18	Nippon Soda Co Ltd	ピリミジン誘導体、その製造方法及び農園芸用殺菌剤
US5238248A (en) *	1989-08-10	1993-08-24	Alvin G. & Co.	Scoring mechanism for a pinball machine
DE4112533A1 (de) *	1991-04-17	1992-10-22	Bayer Ag	Verfahren zur herstellung von enantiomerenreinen substituierten (chinolin-2-yl-methoxy)phenyl-essigsaeuren
DE4200954A1 (de) *	1991-04-26	1992-10-29	Bayer Ag	Heterocyclisch substituierte phenylessigsaeurederivate
US5585490A (en) *	1991-10-08	1996-12-17	Neurogen Corporation	Certain cycloalkyl and azacycloalkyl pyrrolopyrimidines; a new class of GABA brain receptor ligands
DE4309968A1 (de) *	1993-03-26	1994-09-29	Bayer Ag	Phenylglycinamide von heterocyclisch substituierten Phenylessigsäurederivaten
JPH06220059A (ja) *	1993-01-28	1994-08-09	Tanabe Seiyaku Co Ltd	縮合ピリミジン誘導体及びその製法
DE4435477A1 (de) *	1994-10-04	1996-04-11	Bayer Ag	Cycloalkano-indol- und -azaindol-derivate

1996
- 1996-04-18 DE DE19615265A patent/DE19615265A1/de not_active Withdrawn
1997
- 1997-04-07 EP EP97105706A patent/EP0802198A3/fr not_active Ceased
- 1997-04-10 JP JP9106814A patent/JPH1036372A/ja active Pending
- 1997-04-11 US US08/837,076 patent/US5786361A/en not_active Expired - Fee Related
- 1997-04-15 CA CA002202703A patent/CA2202703A1/fr not_active Abandoned

Cited By (3)

* Cited by examiner, † Cited by third party
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JP2003503342A (ja) *	1999-06-25	2003-01-28	バイエルアクチェンゲゼルシャフト	ＭＴＰ阻害剤とＨＭＧ−ＣｏＡ還元酵素阻害剤との組み合わせ並びに薬剤におけるその使用
JP2003535888A (ja) *	2000-06-21	2003-12-02	バイエルアクチェンゲゼルシャフト	食後のトリグリセリドに富んだリポタンパク質粒子（ｐｐｔｒｌ）の数を低下させるための、ミクロソームのトリグリセリド輸送タンパク質（ｍｔｐ）インヒビターの使用
WO2025239340A1 (fr) *	2024-05-14	2025-11-20	日本農薬株式会社	Composé amide ou sel de celui-ci, microbicide agricole et horticole contenant ledit composé ou sel, et procédé d'utilisation dudit microbicide

Also Published As

Publication number	Publication date
CA2202703A1 (fr)	1997-10-18
US5786361A (en)	1998-07-28
DE19615265A1 (de)	1997-12-04
EP0802198A2 (fr)	1997-10-22
EP0802198A3 (fr)	1998-04-15

Publication	Publication Date	Title
KR100355986B1 (ko)	2003-01-06	시클로알카노-인돌및-아자인돌유도체
US6200971B1 (en)	2001-03-13	Bicyclic heterocyclic compounds
JPH09216884A (ja)	1997-08-19	置換キサンチン類
JPH1059914A (ja)	1998-03-03	ヘテロ−結合フエニルグリシノールアミド
JPH07188165A (ja)	1995-07-25	５，６−双環性グリコプロテインＩＩｂ／ＩＩＩａ拮抗剤
JPH1059972A (ja)	1998-03-03	新規なピリミド［１，２−ａ］インドール類
JPH1053578A (ja)	1998-02-24	複素環で置換されたフエニルグリシノールアミド
JPH08253448A (ja)	1996-10-01	複素環式置換基を有するオキシ−フエニル−（フエニル）グリシノールアミド
US5786361A (en)	1998-07-28	Pyridazino-, pyrimido-, pyrazino- and triazinoindoles, -pyrrolocycloalkenes or pyrrolooxocycloalkenes, or pyridopyrrolylpyrido compounds, compositions containing them, and use thereof to treat atherosclerosis
KR20000052978A (ko)	2000-08-25	5Ｈ-피롤로[2,1-ｃ][1,4]-벤조디아제핀의 3-카복스아미드 유도체
US6235770B1 (en)	2001-05-22	Indolyl-substituted phenylacetic acid derivatives
JPH09110866A (ja)	1997-04-28	複素環式アリール−、アルキル−およびシクロアルキルアセトアミド類
JPH1059915A (ja)	1998-03-03	ベンジルオキシ−置換フエニルグリシノールアミド
US6194424B1 (en)	2001-02-27	Arylacetamides and their use as medicaments
US5849751A (en)	1998-12-15	Amides and sulphonamides of benzylamines having heterocyclic substituents
JPWO2000071502A1 (ja)	2002-12-17	ヒドラジド誘導体
MXPA97002445A (en)	1998-07-03	New pyrimid [1,2-] indo
JPWO2001074817A1 (ja)	2003-07-15	ヒドラジド誘導体
HK1005139B (en)	2004-05-21	Cycloalkano-indole-and-azaindole derivatives
JPWO2000020417A1 (ja)	2002-01-08	縮合ピリダジン化合物、その製造法および用途

JPH1036372A - 新規なピリダジノ−、ピリミド−、ピラジノ−およびトリアジノ−インドール類 - Google Patents

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